Hydrochloric Acid → HCID 178492201, compound

HRID 511004Notes

Reaction equation

HRID 511004 reaction equation
[Cl:1][C:2]1[C:3]([F:35])=[C:4]([C:22]2[CH2:23][CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][CH:27]=2)[C:5]([O:20][CH3:21])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH3:9])[CH:7]=1.Cl.CCN(C(C)C)C(C)C.CS(Cl)(=O)=O>O1CCOCC1.C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[C:3]([F:35])=[C:4]([C:22]2[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=2)[C:5]([O:20][CH3:21])=[C:6]([CH:8]([NH:10][C:11]2[N:19]=[CH:18][N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH3:9])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178492202HCID 178492202, compound

Product 1

HCID 178492201HCID 178492201, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Into a microwave vial was added tert-butyl 4-{3-chloro-2-fluoro-6-methoxy-5-[1-(9H-purin-6-ylamino)ethyl]phenyl}-3,6-dihydropyridine-1(2H)-carboxylate (10.5 mg, 0.021 mmol) and 4.0 M HCl in 1,4-dioxane (1.0 mL). The mixture was stirred for 30 min and evaporated. Methylene chloride (1.0 mL) and DIPEA (15.6 μL, 0.090 mmol) were added followed by methanesulfonyl chloride (4.8 pt, 0.063 mmol). The mixture was stirred for 15 minutes. The solvents were evaporated. 1 N sodium hydroxide solution (1.0 mL) and methanol (1.0 mL) were added and the mixture was stirred for 1 hour. The solvents were evaporated and purification by preparative LC/MS (pH 10) gave the desired compound (4.0 mg, 40%). LCMS calculated for C20H23ClFN6O3S (M+H)+: m/z=481.1. found: 481.0. 1H NMR (DMSO-d6, 500 MHz) δ 12.88 (1H, br s), 8.18 (2H, m), 7.63 (1H, m), 5.91 (1H, m), 5.78 (1H, br s), 3.94 (5H, m), 3.40 (2H, m), 2.98 (3H, s), 2.55 (2H, m), 2.39 (2H, m), 1.42 (3H, m).

Workup

  1. customevaporated
  2. stirringThe mixture was stirred for 15 minutes
  3. customThe solvents were evaporated
  4. addition1 N sodium hydroxide solution (1.0 mL) and methanol (1.0 mL) were added
  5. stirringthe mixture was stirred for 1 hour
  6. customThe solvents were evaporated
  7. custompurification by preparative LC/MS (pH 10)

Sources & evidence

ORD record
ord-d01efbf8570944aba5c5dec44ce762ee
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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